This research is directed towards the synthesis of a number of naturally occurring quinones which show antineoplastic as well as antibiotic properties. The target molecules are all compounds which are classed as potential bioreductive alkylating agents. Such compounds are viewed as potential drugs which become activated towards covalent bond formation with a nucleophilic center on a biomolecule only subsequent to an in vivo reduction. As a result, this research project has as its fundamental objective the synthesis of both natural products and synthetic analogs which could function by such a mechanism. The specific synthetic objectives include mitomycin C, adriamycin, and nanaomycin. The synthetic routes under investigation have been designed so that they are very versatile and will thus allow the construction of a large number of compounds which possess these structural features deemed necessary for biological activity.